FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2914074818> ?p ?o ?g. }

• W2914074818 endingPage "492" @default.
• W2914074818 startingPage "487" @default.
• W2914074818 abstract "Phospha-Mannich reactions of benzyl carbamate, aldehydes, and methyl dichlorophosphite followed by aminolysis with amino acid esters or alcoholysis with hydroxyl acid esters produce N-Cbz(benzyloxycarbonyl)-protected phosphonopeptides or phosphonodepsipeptides. However, similar reactions do not work when Cbz-amino amides are used instead of the carbamate. Phospha-Mannich reactions of N-Cbz-amino amides/2-(Cbz-amino)alkanesulfonamides, aldehydes, and dichloroarylphosphines and subsequent aminolysis with amino acid esters or alcoholysis with hydroxyl acid esters yield phosphinopeptides or phosphinodepsipeptides and hybrid sulfonophosphinopeptides or sulfonophosphinodepsipeptides. The different reactivities and mechanistic insights are rationalized that the α-amino alcohols generated from aldehydes and amides/sulfonamides show weaker nucleophilicity than those generated from aldehydes and benzyl carbamate. They can react with stronger electrophilic dichloroarylphosphines rather than weaker electrophilic methyl dichlorophosphite. The nucleophilicity of α-amino alcohols (amine reagents, carbamates, amides, and sulfonamides) and the electrophilicity of phosphorus reagents (dichloroarylphosphines and ethyl dichlorophosphite) control the reactivity of the phospha-Mannich reactions. Phosphorus trichloride is also efficient phosphorus reagent in the phospha-Mannich reactions because it is stronger electrophile as well." @default.
• W2914074818 created "2019-02-21" @default.
• W2914074818 creator A5046676415 @default.
• W2914074818 date "2019-02-17" @default.
• W2914074818 modified "2023-09-27" @default.
• W2914074818 title "Convergent synthesis of phosphonopeptides via phospha-Mannich reactions: Rationale on reactivity and mechanistic insights" @default.
• W2914074818 cites W1930568816 @default.
• W2914074818 cites W1965559481 @default.
• W2914074818 cites W1968064669 @default.
• W2914074818 cites W1975974172 @default.
• W2914074818 cites W1978478750 @default.
• W2914074818 cites W1990074614 @default.
• W2914074818 cites W1992540539 @default.
• W2914074818 cites W2002876276 @default.
• W2914074818 cites W2006092375 @default.
• W2914074818 cites W2007960999 @default.
• W2914074818 cites W2015036947 @default.
• W2914074818 cites W2023655974 @default.
• W2914074818 cites W2026572945 @default.
• W2914074818 cites W2026761188 @default.
• W2914074818 cites W2029575053 @default.
• W2914074818 cites W2036908573 @default.
• W2914074818 cites W2037402356 @default.
• W2914074818 cites W2043491388 @default.
• W2914074818 cites W2045212783 @default.
• W2914074818 cites W2060570565 @default.
• W2914074818 cites W2061941472 @default.
• W2914074818 cites W2067785467 @default.
• W2914074818 cites W2071883724 @default.
• W2914074818 cites W2081282776 @default.
• W2914074818 cites W2084932201 @default.
• W2914074818 cites W2087355681 @default.
• W2914074818 cites W2120168423 @default.
• W2914074818 cites W2151892885 @default.
• W2914074818 cites W2329427578 @default.
• W2914074818 cites W2378209437 @default.
• W2914074818 cites W2762494500 @default.
• W2914074818 cites W2949768704 @default.
• W2914074818 cites W2950240082 @default.
• W2914074818 cites W2950585236 @default.
• W2914074818 cites W2950624143 @default.
• W2914074818 cites W2951621271 @default.
• W2914074818 cites W2951945078 @default.
• W2914074818 cites W2952496690 @default.
• W2914074818 doi "https://doi.org/10.1080/10426507.2018.1540481" @default.
• W2914074818 hasPublicationYear "2019" @default.
• W2914074818 type Work @default.
• W2914074818 sameAs 2914074818 @default.
• W2914074818 citedByCount "5" @default.
• W2914074818 countsByYear W29140748182020 @default.
• W2914074818 countsByYear W29140748182021 @default.
• W2914074818 crossrefType "journal-article" @default.
• W2914074818 hasAuthorship W2914074818A5046676415 @default.
• W2914074818 hasConcept C142724271 @default.
• W2914074818 hasConcept C155647269 @default.
• W2914074818 hasConcept C161790260 @default.
• W2914074818 hasConcept C178790620 @default.
• W2914074818 hasConcept C178907741 @default.
• W2914074818 hasConcept C185592680 @default.
• W2914074818 hasConcept C204787440 @default.
• W2914074818 hasConcept C2776910235 @default.
• W2914074818 hasConcept C2777998946 @default.
• W2914074818 hasConcept C2779303437 @default.
• W2914074818 hasConcept C2780640045 @default.
• W2914074818 hasConcept C40875361 @default.
• W2914074818 hasConcept C50027330 @default.
• W2914074818 hasConcept C71924100 @default.
• W2914074818 hasConceptScore W2914074818C142724271 @default.
• W2914074818 hasConceptScore W2914074818C155647269 @default.
• W2914074818 hasConceptScore W2914074818C161790260 @default.
• W2914074818 hasConceptScore W2914074818C178790620 @default.
• W2914074818 hasConceptScore W2914074818C178907741 @default.
• W2914074818 hasConceptScore W2914074818C185592680 @default.
• W2914074818 hasConceptScore W2914074818C204787440 @default.
• W2914074818 hasConceptScore W2914074818C2776910235 @default.
• W2914074818 hasConceptScore W2914074818C2777998946 @default.
• W2914074818 hasConceptScore W2914074818C2779303437 @default.
• W2914074818 hasConceptScore W2914074818C2780640045 @default.
• W2914074818 hasConceptScore W2914074818C40875361 @default.
• W2914074818 hasConceptScore W2914074818C50027330 @default.
• W2914074818 hasConceptScore W2914074818C71924100 @default.
• W2914074818 hasFunder F4320321001 @default.
• W2914074818 hasIssue "4-6" @default.
• W2914074818 hasLocation W29140748181 @default.
• W2914074818 hasOpenAccess W2914074818 @default.
• W2914074818 hasPrimaryLocation W29140748181 @default.
• W2914074818 hasRelatedWork W1966380009 @default.
• W2914074818 hasRelatedWork W2021208456 @default.
• W2914074818 hasRelatedWork W2021939235 @default.
• W2914074818 hasRelatedWork W2094142780 @default.
• W2914074818 hasRelatedWork W2123519398 @default.
• W2914074818 hasRelatedWork W2152682168 @default.
• W2914074818 hasRelatedWork W2607483172 @default.
• W2914074818 hasRelatedWork W2952556931 @default.
• W2914074818 hasRelatedWork W3197057116 @default.
• W2914074818 hasRelatedWork W4366774724 @default.
• W2914074818 hasVolume "194" @default.
• W2914074818 isParatext "false" @default.

• next